Sodium Dithionite → HCID 11159758, compound

HRID 603098Notes

Reaction equation

HRID 603098 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH2:12][CH2:13][OH:14].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][CH2:12][CH2:13][OH:14]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 12394444HCID 12394444, compound

Product 1

HCID 11159758HCID 11159758, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(2-chloro-6-nitrophenyl)amino]ethanol (120 g, 0.554 mol) in methanol (1.5 l) at 60° C. is added a solution of Na2S2O4 (85%, 318 g, 1.55 mol) in water (1.12 l) over 20 min. The obtained suspension is stirred at 60° C. for additional 20 min. The decolourized mixture is allowed to cool and concentrated under vacuum. In an ice bath, 800 ml of 1.5 M NaOH solution is added and the mixture is extracted three times with 500 ml of AcOEt. The organic phase is washed with brine and dried over magnesium sulphate. The solvents are evaporated to give the desired product (72.4 g, 70%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under vacuum
  3. additionIn an ice bath, 800 ml of 1.5 M NaOH solution is added
  4. extractionthe mixture is extracted three times with 500 ml of AcOEt
  5. washThe organic phase is washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvents are evaporated

Sources & evidence

ORD record
ord-712c1e66716d4c9a9632fbbc5d680fe6
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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